5-(6-Amino-purin-9-yl)-3-(1-hydroxy-ethyl)-cyclopent-3-ene-1,2-diol

ID: ALA327105

Chembl Id: CHEMBL327105

Cas Number: 138571-54-7

PubChem CID: 472632

Max Phase: Preclinical

Molecular Formula: C12H15N5O3

Molecular Weight: 277.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](O)C1=C[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C12H15N5O3/c1-5(18)6-2-7(10(20)9(6)19)17-4-16-8-11(13)14-3-15-12(8)17/h2-5,7,9-10,18-20H,1H3,(H2,13,14,15)/t5-,7-,9-,10+/m1/s1

Standard InChI Key:  CDKUWLLYHVOVCD-PXMQNUKVSA-N

Alternative Forms

1. Parent:

   

   ALA327105

   (1S,2R,5R)-5-(6-aminopurin-9-yl)-3-[(1R)-1-hydroxyethyl]cyclopent-3-ene-1,2-diol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 277.28

Molecular Weight (Monoisotopic): 277.1175

AlogP: -1.01

#Rotatable Bonds: 2

Polar Surface Area: 130.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.08

CX Basic pKa: 4.10

CX LogP: -1.77

CX LogD: -1.77

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.52

Np Likeness Score: 0.63

References

1. Shuto S, Obara T, Toriya M, Hosoya M, Snoeck R, Andrei G, Balzarini J, De Clercq E..  (1992)  New neplanocin analogues. 1. Synthesis of 6'-modified neplanocin A derivatives as broad-spectrum antiviral agents.,  35  (2): [PMID:1732550] [10.1021/jm00080a018]

2. Shuto S, Obara T, Kosugi Y, Saito Y, Toriya M, Yaginuma S, Shigeta S, Matsuda A.  (1994)  New neplanocin analogues. III. 6R-configuration is essential for the antiviral activity of 6-C-methyl-3-deazaneplanocin a's,  4  (4): [10.1016/S0960-894X(01)80163-3]

3. Shuto S, Minakawa N, Niizuma S, Kim HS, Wataya Y, Matsuda A..  (2002)  New neplanocin analogues. 12. Alternative synthesis and antimalarial effect of (6'R)-6'-C-methylneplanocin A, a potent AdoHcy hydrolase inhibitor.,  45  (3): [PMID:11806727] [10.1021/jm010374i]

4. Singh K, Joshi P, Mahar R, Baranwal P, Shukla SK, Tripathi R, Tripathi RP..  (2018)  Synthesis and antiplasmodial activity of purine-based C-nucleoside analogues.,  9  (7): [PMID:30109012] [10.1039/C8MD00098K]

Source

Source(1):

• Scientific Literature